Organic conversion

Ethanol to fluoroethane

2 steps: substitution, then Swarts reaction

Class 12, Chapter 6 Haloalkanes and Haloarenes

Alternative routes (4)

Ethanol → Bromoethane → Fluoroethane
1. Ethanol to bromoethane: red P + Br₂ (PBr₃).
2. Bromoethane to fluoroethane: AgF (or Hg₂F₂, CoF₂, SbF₃).
Ethanol → Ethene → Bromoethane → Fluoroethane
1. Ethanol to ethene: conc. H₂SO₄, 443 K.
2. Ethene to bromoethane: HBr.
3. Bromoethane to fluoroethane: AgF (or Hg₂F₂, CoF₂, SbF₃).
Ethanol → Ethene → Chloroethane → Fluoroethane
1. Ethanol to ethene: conc. H₂SO₄, 443 K.
2. Ethene to chloroethane: HCl.
3. Chloroethane to fluoroethane: AgF (or Hg₂F₂, CoF₂, SbF₃).
Ethanol → Ethene → Ethane → Chloroethane → Fluoroethane
1. Ethanol to ethene: conc. H₂SO₄, 443 K.
2. Ethene to ethane: H₂, Ni (or Pt, Pd).
3. Ethane to chloroethane: Cl₂, UV light.
4. Chloroethane to fluoroethane: AgF (or Hg₂F₂, CoF₂, SbF₃).

Why these reagents

Reagent and reason, step by step

Step 1: Ethanol to chloroethane: SOCl₂ Thionyl chloride gives the pure alkyl chloride because SO₂ and HCl leave as gases.
Step 2: Chloroethane to fluoroethane: AgF (or Hg₂F₂, CoF₂, SbF₃) Swarts reaction: the way to make an alkyl fluoride from a chloride.

Questions

How many steps does it take to convert ethanol to fluoroethane?

2 steps: Ethanol, then chloroethane, then fluoroethane.

Which named reaction is used to convert ethanol to fluoroethane?

Swarts reaction. Alkyl fluorides are made by heating an alkyl chloride or bromide with a metallic fluoride such as AgF, Hg2F2, CoF2 or SbF3.

What is the reagent for step 1 of ethanol to fluoroethane?

Ethanol to chloroethane: SOCl₂. Thionyl chloride gives the pure alkyl chloride because SO₂ and HCl leave as gases.